Methyl iodide → tert-Butyl 3-methoxyazetidine-1-carboxylate

HRID 20572노트

반응식

HRID 20572 반응식
[H-].[Na+].[OH:3][CH:4]1[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5]1.I[CH3:16]>C1COCC1>[CH3:16][O:3][CH:4]1[CH2:5][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:7]1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylate

생성물 1

HCID 22243050tert-Butyl 3-methoxyazetidine-1-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Sodium hydride (60% dispersion in oil) (83 mg, 3.46 mmol) was added to tert-butyl 3-hydroxyazetidine-1-carboxylate (J Med chem., 44(1), 2001, 94) (0.3 g, 1.73 mmol) in THF (10 mL), at 0° C., under argon. The reaction was stirred for 30 mins then iodomethane (0.13 mL, 4.15 mmol) added. After stirring at 0° C. for 30 mins and at RT for 3 hours the volatiles were removed in vacuo. Ethyl acetate (40 mL) was added and the mixture washed with brine (40 mL), dried (MgSO4), filtered, and reduced in vacuo to give the desired compound. (0.32 g). 1H NMR δ (CDCl3): 1.42 (s, 9H), 3.27 (s, 3H), 3.81 (m, 2H), 4.06 (m, 2H), 4.11 (m, 1H).

후처리

  1. stirringAfter stirring at 0° C. for 30 mins and at RT for 3 hours the volatiles
  2. customwere removed in vacuo
  3. additionEthyl acetate (40 mL) was added
  4. washthe mixture washed with brine (40 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered

출처 및 근거

ORD 기록
ord-e574ce53bebc4e02b90a060439e2a85e
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745475B2

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